Phenoxyphenylisothioureas, production thereof and use thereof in pest control, and phenoxyphenylthioureas as intermediates for the production of the phenoxyphenylisothioureas and use thereof in pest control

ABSTRACT

The invention relates to N-phenoxyphenylisothioureas of the formula ##STR1## wherein each R 1 , R 2  and R 3  is hydrogen, halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, trifluoromethyl or nitro, each of R 4  and R 5  is C 2  -C 4  alkyl, R 6  is C 1  -C 6  alkyl, C 3  -C 6  alkenyl or C 3  -C 5  alkynyl, R 7  is C 1  -C 10  alkyl, C 3  -C 5  alkenyl or C 3  -C 6  cycloalkyl, and R 8  is hydrogen or C 1  -C 10  alkyl. The invention further relates to the production of these compounds and their use in pest control, as well as to phenoxyphenylthioureas as intermediates for the production of the N-phenoxyphenylisothioureas of the invention.

The present invention relates to N-phenoxyphenylisothioureas, theproduction thereof, pesticidal compositions containing them, and usethereof for controlling pests of animals and plants.

The N-phenoxyphenylisothioureas have the formula ##STR2## wherein eachof R₁, R₂ and R₃ is hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy,trifluoromethyl or nitro, each of R₄ and R₅ is C₂ -C₄ alkyl, R₆ is C₁-C₆ alkyl, C₃ -C₆ alkenyl or C₃ -C₅ alkynyl, R₇ is C₁ -C₁₀ alkyl, C₃ -C₅alkenyl or C₃ -C₆ cycloalkyl, and R₈ is hydrogen or C₁ -C₁₀ alkyl.

Halogen in the above definition denotes fluorine, chlorine, bromine oriodine, with chlorine being preferred.

Alkyl, alkoxy, alkenyl and alkynyl groups R₁ to R₈ can be straight chainor branched. Examples of such groups comprise methyl, methoxy, ethyl,propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl,n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl and their isomers, allyl,methallyl, and propargyl.

Preferred cycloalkyl groups R₇ are cyclopropyl and cyclohexyl.

Preferred compounds on account of their activity are those of theformula I wherein R₁ is hydrogen, chlorine, methoxy, trifluoromethyl ornitro, each of R₂ and R₃ is hydrogen or chlorine, each of R₄ and R₅ isethyl, isopropyl, isobutyl, sec-butyl or tert-butyl, R₆ is C₁ -C₆ alkyl,allyl or propargyl, R₇ is C₁ -C₆ alkyl, cyclopropyl or cyclohexyl, andR₈ is hydrogen.

Especially preferred compounds, however, are those of the formula Iwherein R₁ is hydrogen, chlorine or trifluoromethyl, R₂ is hydrogen orchlorine, R₃ is hydrogen, each of R₄ and R₅ is isopropyl, or R₄ is ethyland R₅ is sec-butyl, R₆ is methyl, R₇ is tert-butyl or isopropyl, and R₈is hydrogen.

The compounds of formula I also exist in the form of acid additionsalts, e.g. mineral salts, and can be used in the form of their salts inthe practice of this invention. Accordingly, the invention is to beconstrued as comprising both the free compounds of formula I and theirnon-toxic acid addition salts.

The compounds of the formula I can be converted to their acid additionsalts by procedures known per se. Suitable acids for forming additionsalts are for example: hydrochloric acid, hydrobromic acid, hydriodicacid, nitric acid, phosphoric acid, sulfuric acid, acetic acid,propionic acid, butyric acid, valeric acid, oxalic acid, malonic acid,succinic acid, malic acid, maleic acid, fumaric acid, lactic acid,tartaric acid, citric acid, benzoic acid, phthalic acid, cinnamic acidand salicyclic acid.

The compounds of formula I can be obtained by methods analogous to knownones, by reacting e.g. a thiourea of the formula ##STR3## with a halideof the formula

    R.sub.6 --Hal                                              (III)

in which formulae II and III above R₁ to R₈ are as defined for formula Iand Hal is a halogen atom, especially a chlorine or bromine atom.

The process is conveniently carried out in the temperature range from 0°to 100° C., under normal or slightly elevated pressure, and preferablyin the presence of a solvent or diluent which is inert to the reactants.Examples of suitable solvents or diluents are ethers and etherealcompounds such as diethyl ether, diisopropyl ether, dioxane andtetrahydrofurane; aromatic hydrocarbons such as benzene, toluene andxylenes; and ketones such as acetone, methyl ethyl ketone andcyclohexanone.

The starting compounds of the formula II are new. They can be readilyobtained from known precursors by reacting e.g. an isothiocyanate of theformula IV ##STR4## with an amine of the formula V

    R.sub.7 --NH.sub.2                                         (V)

in which formulae IV and V above R₁ to R₅ and R₇ are as previouslydefined (cf. Example 1).

The process for obtaining the starting materials of formula II ispreferably carried out in the presence of a solvent or diluent which isinert to the reactants, in the temperature range from 0° to 100° C. andunder normal pressure. Suitable solvents and diluents for this processare those specified above as suitable for the process for obtaining thefinal products of formula I.

The compounds of formula I and the starting materials of formula II aresuitable for controlling pests of animals and plants.

In particular, the compounds of formulae I and II are suitable forcontrolling insects, phytopathogenic mites and ticks, e.g. of the orderLepidoptera, Coleoptera, Homoptera, Diptera, Acarina, Thysanoptera,Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera,Psocoptera and Hymenoptera.

In particular, the compounds of formulae I and II are suitable forcontrolling plant-destructive insects, especially plant-destructivefeeding insects, in ornamentals and useful plants, preferably in cottonplantations (e.g. Spodoptera littoralis and Heliothis virescens) and invegetables (e.g. Leptinotarsa decemlineata).

Compounds of formulae I and II are also very effective against flies,e.g. Musca domestica and mosquito larvae.

The acaracidal activity of the compounds of formula I also extends toboth plant-destructive acarids (mites e.g. of the familiesTetranychidae, Tarsonemidae, Eriophydae, Tyroglyphidae andGlycyphagidae) and against ectoparasitic acarids (mites and ticks e.g.of the families Ixodidae, Argasidae, Sarcoptidae and Dermanyssidae)which are harfmul to productive livestock.

Compounds of the formulae I and II are also combined with particularadvantage with substances which exert a synergistic or potentiatingeffect. Examples of such compounds include: piperonyl butoxide, propynylether, propynyl oximes, propynyl carbamates and propynyl phosphates,2-(3,4-methylenedioxyphenoxy)-3,6,9-trioxaundecane (Sesamex orSesoxane), S,S,S-tributylphosphorotrithioate,1,2-methylenedioxy-4(2-(octylsulfinyl)-propyl)-benzene.

The compounds of formulae I and II can be employed in known manner andin unmodified form or together with the adjuvants conventionally used inthe art of formulation, e.g. emulsifiable concentrates, suspensionconcentrates, directly sprayable or dilutable solutions, diluteemulsions, wettable powders, soluble powders, dusts, granules, and alsomicroencapsulations in polymer substances and the like. The methods ofapplication, such as spraying, atomising, dusting, scattering orpouring, depend entirely on the end-use requirements, in whichconnection it must be ensured that the biological activity of thecompounds of formulae I or II is not substantially influenced by themethod of application or by the nature and amount of the adjuvantsemployed for preparing the formulation.

The preparations are produced in known manner, for example by intimatelymixing and/or grinding the active ingredients with extenders, i.e. withsolvents or solid carriers, and optionally with the use ofsurface-active substances (surfactants). Suitable solvents are aromatichydrocarbons, preferably the fractions C₈ to C₁₂, i.e. xylene mixturesup to substituted naphthalenes, aliphatic hydrocarbons such ascyclohexane or paraffins, alcohols and glycols, as well as ethers andesters thereof, strongly polar solvents, such as dimethyl sulfoxide ordimethyl formamide, and also water. The solid carriers used, e.g. fordusts and dispersible powders, are mostly natural mineral fillers. Forchemical purposes, suitable solid carriers are in particular calcite,talcum, kaolinite, montmorillonite and attapulgite. In order to improvethe physical properties, it is also possible to use highly dispersedsilicic acids or highly dispersed absorbent polymers. Suitablegranulated carriers are porous types, e.g. pumice, broken brick,sepiolite and bentonite; and suitable nonsorbent carriers are materialssuch as calcite or sand. In addition, it is also possible to use a largenumber of pregranulated materials of inorganic or organic nature,extending from dolomite to pulverised nutshells or corncobs.

Depending on the polarity of the compound of the formula I or II to beformulated, suitable surface-active substances are nonionic, cationicand/or anionic surfactants having good emulsifying, dispersing andwetting properties.

Examples of suitable anionic surfactants are: quaternary ammoniumcompounds such as cetyltrimethylammonium bromide. Examples of suitableanionic surfactants are: soaps, salts of aliphatic monoesters ofsulfuric acid, such as sodium lauryl sulfate, salts of sulfonatedaromatic compounds, for example sodium dodecylbenzenesulfonate, sodium,calcium and ammonium ligninsulfonate, butylnaphthalenesulfonate and amixture of the sodium salts of diisopropyl- andtriisopropylnaphthalenesulfonate. Examples of suitable non-ionicsurfactants are the condensation products of ethylene oxide with fattyalcohols, for example oleyl alcohol or cetyl alcohol, or withalkylphenols, such as octylphenol, nonylphenol and octylcresol. Othernon-ionic compounds are the partial esters derived from long-chain fattyacids and hexite anhydrides, and the condensation products of thesepartial esters with ethylene oxide, or lecithins.

The non-ionic, anionic and cationic surfactants commonly used in the artof formulation are described, inter alia, in the following publications:"Mc Cutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp.,Ringewood, New Jersey; Sisely and Wood, "Encyclopedia of Surface ActiveAgents", Chemical Publishing Co., New York.

The formulations as a rule contain 0.1 to 99%, especially 0.1 to 95%, ofcompound of the formula I or II, and at least 0 to 25% of a surfactant,as well as 1 to 99.9% of a solid or liquid adjuvant.

The formulations can also contain additives such as stabilisers,antifoams, viscosity regulators, binders, adhesives, and alsofertilisers, to produce special effects.

The compounds (active ingredients) of the formula I or II can beformulated for example as follows: (throughout, percentages are byweight)

FORMULATION EXAMPLES FOR LIQUID ACTIVE INGREDIENTS OF THE FORMULA I ORII Emulsifiable concentrates

    ______________________________________                                        (a)    active ingredient      20%                                                    calcium dodecylbenzenesulfonate                                                                       5%                                                    castor oil polyglycol ether                                                   (36 moles of ethylene oxide)                                                                          5%                                                    xylene mixture         70%;                                            (b)    active ingredient      40%                                                    calcium dodecylbenzenesulfonate                                                                       8%                                                    tributylphenolpolyglycol ether                                                (30 moles of ethylene oxide)                                                                         12%                                                    cyclohexanone          15%                                                    xylene mixture         25%;                                            (c)    active ingredient      50%                                                    tributylphenolpolyglycol ether                                                                        4.2%                                                  calcium dodecylbenzenesulfonate                                                                       5.8%                                                  cyclohexanone          20%                                                    xylene mixture         20%.                                            ______________________________________                                    

Emulsions of any required concentration can be produced from suchconcentrates by dilution with water.

    ______________________________________                                        Solutions                                                                     ______________________________________                                        (a)    active ingredient      80%                                                    ethylene glycol monomethyl ether;                                                                    20%                                             (b)    active ingredient      10%                                                    polyethylene glycol 400                                                                              70%                                                    N-methyl-2-pyrrolidone;                                                                              20%                                             (c)    active ingredient       5%                                                    epoxidised vegetable oil                                                                              1%                                                    ligroin (boiling range 160-190° C.);                                                          94%                                             (d)    active ingredient      95%                                                    epoxidised vegetable oil                                                                              5%.                                            ______________________________________                                    

These solutions are suitable for application in the form of microdrops.

    ______________________________________                                        Granules                                                                      ______________________________________                                        (a)     active ingredient      5%                                                     kaolin (0.2-0.8 mm)   94%                                                     highly dispersed silicic acid                                                                        1%                                             (b)     active ingredient     10%                                                     attapulgit            90%.                                            ______________________________________                                    

The active ingredient is dissolved in methylene chloride, the solutionis sprayed onto the carrier, and the solvent is subsequently evaporatedoff in vacuo.

    ______________________________________                                        Dusts                                                                         ______________________________________                                        (a)     active ingredient                                                                              2%                                                           highly dispersed silicic acid                                                                  1%                                                           talcum           97%                                                  (b)     active ingredient                                                                              5%                                                           highly dispersed silicic acid                                                                  5%                                                           kaolin (finely divided)                                                                        90%.                                                 ______________________________________                                    

Dusts which are ready for use are obtained by intimately mixing thecarriers with the active ingredient.

FORMULATION EXAMPLES FOR SOLID ACTIVE INGREDIENTS OF THE FORMULA I OR IIWettable powders

    ______________________________________                                        (a)   active ingredient      20%                                                    sodium ligninsulfonate 5%                                                     sodium laurylsulfate   3%                                                     silicic acid           5%                                                     kaolin                 67%                                              (b)   active ingredient      60%                                                    sodium ligninsulfonate 5%                                                     sodium diisobutylnaphthalenesulfonate                                                                6%                                                     octylphenol polyglycol ether                                                  (7-8 moles of ethylene oxide)                                                                        2%                                                     highly dispersed silicic acid                                                                        27%.                                             ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        Emulsifiable concentrate                                                      ______________________________________                                        active ingredient     10%                                                     octylphenol polyglycol ether                                                  (4-5 moles of ethylene oxide)                                                                       3%                                                      calcium dodecylbenzenesulfonate                                                                     3%                                                      castor oil polyglycol ether                                                   (36 moles of ethylene oxide)                                                                        4%                                                      cyclohexanone         30%                                                     xylene mixture        50%.                                                    ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        Dusts                                                                         ______________________________________                                        (a)     active ingredient                                                                            5%                                                             talcum         95%                                                    (b)     active ingredient                                                                            8%                                                             kaolin (finely divided)                                                                      92%.                                                   ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carriers, and grinding the mixture in a suitablemill.

    ______________________________________                                        Extruder granulate                                                            ______________________________________                                        active ingredient  10%                                                        sodium ligninsulfonate                                                                           2%                                                         carboxymethylcellulose                                                                           1%                                                         kaolin (finely divided)                                                                          87%.                                                       ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a stream of air.

    ______________________________________                                        Coated granulate                                                              ______________________________________                                        active ingredient  3%                                                         polyethylene glycol 200                                                                          3%                                                         kaolin (0.3-0.8 mm)                                                                              94%.                                                       ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        Suspension concentrate                                                        ______________________________________                                        active ingredient         40%                                                 ethylene glycol           10%                                                 nonylphenol polyglycol ether                                                  (15 moles of ethylene oxide)                                                                             6%                                                 sodium ligninsulfonate    10%                                                 carboxymethylcellulose     1%                                                 formalin (37% formaldehyde solution)                                                                     0.2%                                               silicone oil in the form of a 75%                                             emulsion                   0.8%                                               water                     32%.                                                ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

Example 1 (a) Production of 2,6-diisopropyl-4-phenoxyaniline

48.9 g of phenol are dissolved in 500 ml of xylene, and to this solutionare added 30.2 g of pulverised potassium hydroxide in an atmosphere ofnitrogen. The reaction mixture is stirred and heated to boiling point,while continuously distilling off the water that is formed. Afteraddition of 0.6 g of copper chloride and 100 g of2,6-diisopropyl-4-bromoaniline, the mixture is stirred for 8 hours at150°-155° C., then cooled, and filtered with suction. The filtrate iswashed with 15% sodium hydroxide solution (150 ml) and with two 150 mlportions of water. The organic phase is separated and dried over sodiumsulfate. The solvent is removed by distillation and the product isdistilled, affording the compound of the formula ##STR5## with a boilingpoint of 103°-104° C./0.01 torr and a melting point of 71°-72° C. (afterrecrystallisation from hexane).

The following anilines are also obtained in analogous manner: ##STR6##

(b) Production of N-(2,6-diisopropyl-4-phenoxyphenyl)isothiocyanate

8.9 g of thiophosgene and 13.7 g of calcium carbonate are stirred in 60ml of methylene chloride and 35 ml of water. Then 17.4 g of2,6-diisopropyl-4-phenoxyaniline are added dropwise at 0° to 5° C. tothis mixture. The reaction mixture is brought to the boil and stirredfor 2 hours at reflux. After it has cooled, the mixture is filtered. Theorganic phase is separated from the filtrate, washed with two 50 mlportions of water, dried over sodium sulfate and concentrated. The crudeproduct (oil) is used without purification for further reaction.

The following compounds are obtained in analogous manner: ##STR7##

(c) Production of compounds of the formula II

19.2 g of N-2,6-diisopropyl-4-phenoxyphenylisothiocyanate are dilutedwith 10 ml of toluene and then 13.8 g of tert-butylamine are added. Thereaction mixture is then stirred for 12 hours at 20°-25° C. The reactionmixture is concentrated and the residue is recrystallised from hexane,affording the compound of the formula ##STR8##

The following compounds are obtained in analogous manner:

    __________________________________________________________________________     ##STR9##                                                                     R'       R"   R'"   R.sup.iv                                                                           R.sup.v                                              __________________________________________________________________________    C.sub.4 H.sub.9 (tert.)                                                                C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-Cl H    m.p.: 146-148° C.                        C.sub.4 H.sub.9 (tert.)                                                                C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  3-CF.sub.3                                                                         H    m.p.: 83-85° C.                          C.sub.4 H.sub.9 (tert.)                                                                C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H    m.p.: 91-92° C.                          C.sub.4 H.sub.9 (tert.)                                                                C.sub.2 H.sub.5                                                                    C.sub.3 H.sub.7(i)                                                                  4-Cl H    m.p.: 127-129° C.                        C.sub.3 H.sub.7(i)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 187° C.                            C.sub.4 H.sub.9 (tert.)                                                                C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 178° C.                            C.sub.4 H.sub.9 (tert.)                                                                C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-CH.sub.3                                                                         H    m.p.: 168-170° C.                        C.sub.3 H.sub.7(i)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-CH.sub.3                                                                         H    m.p.: 146-147° C.                        CH.sub.3 C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 130-131° C.                        C.sub.2 H.sub.5                                                                        C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 148-149° C.                        C.sub.3 H.sub.7(n)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 121-122° C.                        C.sub.3 H.sub.7(i)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 160-161° C.                        C.sub.4 H.sub.9(n)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 117-119° C.                        C.sub.4 H.sub.9(i)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 152-153° C.                        C.sub.4 H.sub.9 (sec.)                                                                 C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 157-158° C.                        C.sub.5 H.sub.11(n)                                                                    C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H    m.p.: 121- 122° C.                       CH.sub.3 C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    CH.sub.3                                                                           m.p.: 149-150° C.                        C.sub.2 H.sub.5                                                                        C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    C.sub.2 H.sub.5                                                                    m.p.: 161-162° C.                        C.sub.3 H.sub.7(n)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    C.sub.3 H.sub.7(n)                                                                 m.p.: 152-153° C.                        C.sub.4 H.sub.9(n)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    C.sub.4 H.sub.9(n)                                                                 m.p.: 153-154° C.                        C.sub.4 H.sub.9 (sec.)                                                                 C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-CH.sub.3                                                                         H    m.p.: 156-157° C.                        CH.sub.3 C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 156-157° C.                        C.sub.2 H.sub.5                                                                        C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 154-155° C.                        C.sub.3 H.sub.7(n)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 155-156° C.                        C.sub.4 H.sub.9(i)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 112-113° C.                        C.sub.4 H.sub.9 (sec.)                                                                 C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub. 3                                                                       H    m.p.: 170-171° C.                        C.sub.7 H.sub.15(n)                                                                    C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 95-98° C.                          C.sub.3 H.sub.7(i)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 187° C.                             ##STR10##                                                                             CH.sub.3                                                                           C.sub.3 H.sub.7(i)                                                                  4-Cl H    m.p.: 143-145° C.                         ##STR11##                                                                             C.sub.2 H.sub.5                                                                    C.sub.3 H.sub.7(i)                                                                  4-Cl H    m.p.: 80-85° C.                          CH.sub.3 C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H    m.p.: 109-110° C.                        C.sub.3 H.sub.7(i)                                                                     C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              H    H    m.p.: 107-110° C.                        C.sub.4 H.sub.9 (tert.)                                                                C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              H    H    m.p.: 97-100° C.                         C.sub.4 H.sub.9(n)                                                                     C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-OCH.sub.3                                                                        H    m.p.: 143-144° C.                        C.sub.6 H.sub.13(n)                                                                    C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H                                                    C.sub.7 H.sub. 15(n)                                                                   C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H                                                    C.sub.10 H.sub.21(n)                                                                   C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  H    H                                                    C.sub.4 H.sub.9 (tert.)                                                                CH.sub.3                                                                           C.sub.3 H.sub.7(i)                                                                  4-Cl H                                                     ##STR12##                                                                             CH.sub.3                                                                           C.sub.4 H.sub.9 (tert.)                                                             4-Cl H                                                    C.sub.4 H.sub.9 (tert.)                                                                CH.sub.3                                                                           C.sub.4 H.sub.9 (tert.)                                                             4-Cl H                                                    C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                    C.sub.3 H.sub.7(n)                                                                     C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                    C.sub.3 H.sub.7(i)                                                                     C.sub.2 H.sub.2                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                     ##STR13##                                                                             C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                    C.sub.4 H.sub.9(n)                                                                     C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                    C.sub.4 H.sub.9(i)                                                                     C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                    C.sub.4 H.sub.9 (sec.)                                                                 C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                     ##STR14##                                                                             C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                     ##STR15##                                                                             C.sub.2 H.sub.5                                                                    C.sub.4 H.sub.9 (sec.)                                                              4-Cl H                                                    C.sub.4 H.sub.9 (tert.)                                                                C.sub.3 H.sub.7(i)                                                                 C.sub.3 H.sub.7(i)                                                                  4-Cl;                                                                              H                                                                        3-Cl                                                      __________________________________________________________________________

(d) Production of the final product

11.54 g of N-2,6-diisopropyl-4-(phenoxyphenyl)-N'-tert-butylthiourea aredissolved in 30 ml of dimethyl formamide, and 5.96 g of methyl iodideare added dropwise to this solution at 40° C. The reaction mixture isallowed to stand for 12 hours at room temperature, then poured into anaqueous solution which is adjusted to and kept at pH 12 with potassiumcarbonate. The aqueous solution is extracted with methylene chloride andthe organic phase is separated and dried over potassium carbonate. Themethylene chloride is removed by distillation. Recrystallisation fromhexane (cooling to -50° C.) yields the compound of the formula ##STR16##with a melting point of 89°-92° C.

The following compounds are also obtained in analogous manner: ##STR17##

    __________________________________________________________________________    R'        R"           R'" R.sup.iv                                                                            R.sup.v                                      __________________________________________________________________________    C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  Cl  m.p.: 120° C.                     C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 86-87° C.                   C.sub.3 H.sub.7(i)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 94-96° C.                   C.sub.3 H.sub.7(i)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.37,5° = 1.5605        C.sub.3 H.sub.7(i)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 106-107° C.                 C.sub.3 H.sub.7(i)                                                                      C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 67-68° C.                   C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 93-94° C.                   C.sub.4 H.sub.9 (tert.)                                                                 C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 114-116° C.                 C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     CH.sub.3                                                                          C.sub.3 H.sub.7(i)                                                                  Cl  m.p.: 99-100° C.                   ##STR18##                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3                                                                          C.sub.3 H.sub.7(i)                                                                  Cl                                           C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     CH.sub.3                                                                          C.sub.4 H.sub.9 (tert.)                                                             Cl                                           C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2CCH  CH.sub.3                                                                          C.sub.4 H.sub.9 (tert.)                                                             Cl                                            ##STR19##                                                                              CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.3 H.sub.7(i)                                                                  Cl                                            ##STR20##                                                                              C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                   C.sub. 3 H.sub.7(i)                                                                 Cl                                           C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.3 H.sub.7(i)                                                                  Cl  m.p.: 65-68° C.                   C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2CCH  C.sub.2 H.sub.5                                                                   C.sub.3 H.sub.7(i)                                                                  Cl                                            ##STR21##                                                                              CH.sub.3     CH.sub.3                                                                          C.sub.3 H.sub.7(i)                                                                  Cl                                           C.sub.3 H.sub.7(i) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 189-190° C.                 C.sub.4 H.sub.9 (sec.)                                                                  CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                     C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2CHCH.sub.2                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 84-86° C.                   C.sub.4 H.sub.9 (tert.) . HI                                                            CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 169-170° C.                 C.sub.4 H.sub.9 (tert.)                                                                 C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 111-113°  C.                C.sub.4 H.sub.9 (tert.) . HBr                                                           CH.sub.2CHCH.sub.2                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  CH.sub.3                                                                          m.p.: 124-126° C.                 CH.sub.3  CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 120-121° C.                 CH.sub.3 . HI                                                                           CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 176-177° C.                 C.sub.2 H.sub.5                                                                         CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 100-102° C.                 C.sub.2 H.sub.5 . HI                                                                    CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 176-177° C.                 C.sub.3 H.sub.7(n)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 76-77° C.                   C.sub.3 H.sub.7(n) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 171-172° C.                 C.sub.3 H.sub.7(i)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 106-107° C.                 C.sub.4 H.sub.9(n)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 70-72°  C.                  C.sub.4 H.sub.9(n) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 142-145° C.                 C.sub.4 H.sub.9(i)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 111-112° C.                 C.sub.4 H.sub.9(i) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 136-140° C.                 C.sub.4 H.sub.9 (sec.)                                                                  CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 83-84° C.                   C.sub.4 H.sub.9 (sec.) . HI                                                             CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                    C.sub.7 H.sub.15(n)                                                                     CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         n.sub.D.sup.35° : 1.5518          C.sub.7 H.sub.15(n) . H                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  OCH.sub.3                                                                         m.p.: 119-122° C.                 CH.sub.3  CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 109-110° C.                 CH.sub.3 . HI                                                                           CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 190-192° C.                 C.sub.2 H.sub. 5                                                                        CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 75-76° C.                   C.sub.2 H.sub.5 . HI                                                                    CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 189-190° C.                 C.sub.3 H.sub.7(n)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5650          C.sub.3 H.sub.7(n)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 190-191° C.                 C.sub.3 H.sub.7(i) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 183-184° C.                 C.sub.4 H.sub.9(n)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.50° : 1.5544          C.sub.4 H.sub.9(n) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 185-187° C.                 C.sub.4 H.sub.9(i)                                                                      CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5569          C.sub.4 H.sub.9(i) . HI                                                                 CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 170-171° C.                 C.sub.4 H.sub.9 (sec.)                                                                  CH.sub.3     C.sub. 3 H.sub.7(i)                                                               C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.50° : 1.5512          C.sub.4 H.sub.9 (sec.) . HI                                                             CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 148-150° C.                 C.sub.5 H.sub.11(n)                                                                     CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5548          C.sub.5 H.sub.11(n) . HI                                                                CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 139-141° C.                 C.sub.6 H.sub.13(n)                                                                     CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5524          C.sub.6 H.sub.13(n) . HI                                                                CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 121-122° C.                 C.sub.7 H.sub.15(n)                                                                     CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5461          C.sub.7 H.sub.15(n) . HI                                                                CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 100-101° C.                 C.sub.10 H.sub.21(n)                                                                    CH.sub.3     C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5392          C.sub.10 H.sub.21(n) . HI                                                               CH.sub.3     C.sub. 3 H.sub.7(i)                                                               C.sub.3 H.sub.7(i)                                                                  H                                            CH.sub.3  CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           CH.sub.3 . HI                                                                           CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  m.p.: 165-170° C.                 CH.sub.3  C.sub.3 H.sub.7(n)                                                                         C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           C.sub.2 H.sub.5                                                                         CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5731          C.sub.2 H.sub.5 . HI                                                                    CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  m.p.: 140-145° C.                 C.sub.2 H.sub.5                                                                         C.sub.4 H.sub.9(n)                                                                         C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           C.sub.3 H.sub.7(n)                                                                      CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5681          C.sub.3 H.sub.7 . HI                                                                    CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  m.p.: 87-90° C.                   C.sub.3 H.sub.7(n) . HI                                                                 CH.sub.2CCH  C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5734          C.sub.3 H.sub.7(i)                                                                      CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5528          C.sub.3 H.sub.7(i) . HI                                                                 CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  m.p.: 130-135° C.                 C.sub.3 H.sub.7(i)                                                                      CH.sub.2CHCH.sub.2                                                                         C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5631           ##STR22##                                                                              CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5721           ##STR23##                                                                              C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5560          C.sub.4 H.sub.9(n)                                                                      CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           C.sub.4 H.sub.9(n) . HI                                                                 CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           C.sub.4 H.sub.9(i)                                                                      CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup. 50° : 1.5563         C.sub.4 H.sub.9(i) . HI                                                                 CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.40° : 1.5734          C.sub.4 H.sub.9(i)                                                                      CH.sub.2CCH  C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           C.sub.4 H.sub.9 (sec.)                                                                  CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5562          C.sub.4 H.sub.9 (sec.) . HI                                                             CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                           C.sub.4 H.sub.9 (sec.)                                                                  CH.sub.2CHCH.sub.2                                                                         C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5547          C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5591          C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2CCH  C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5596           ##STR24##                                                                              CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5643           ##STR25##                                                                              CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl                                            ##STR26##                                                                              CH.sub.2 CCH C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              Cl  n.sub.D.sup.50° : 1.5721          C.sub.4 H.sub.9 (tert.)                                                                 C.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.50° : 1.5750          C.sub.4 H.sub.9 (tert.)                                                                 C.sub.2 H.sub.5 . HI                                                                       C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H                                            C.sub.4 H.sub.9 (tert.)                                                                 C.sub.3 H.sub.7(n)                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 62-63° C.                   C.sub.4 H.sub.9 (tert.)                                                                 C.sub.3 H.sub.7(n) . HI                                                                    C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H                                            C.sub.4 H.sub. 9 (tert.)                                                                C.sub.4 H.sub.9(n)                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 57-60° C.                   C.sub.4 H.sub.9 (tert.)                                                                 C.sub.4 H.sub.9 . HBr                                                                      C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H                                            C.sub.4 H.sub.9 (tert.)                                                                 C.sub.4 H.sub.9(i)                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 80-82° C.                   C.sub.4 H.sub.9 (tert.)                                                                 C.sub.4 H.sub.9(i) . HI                                                                    C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   n.sub.D.sup.40° : 1.5672          C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2CHCH.sub.2                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 78-80° C.                   C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2 CHCH.sub.2 . HBr                                                                  C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H                                            C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2CCH  C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 79-81° C.                   C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.2 CCH . HBr                                                                         C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub. 7(i)                                                                 H                                            C.sub.3 H.sub.7(i)                                                                      CH.sub.2 CHCH.sub.2                                                                        C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H                                            C.sub.3 H.sub.7(i)                                                                      CH.sub.2CHCH.sub.2 . HBr                                                                   C.sub.3 H.sub.7(i)                                                                C.sub.3 H.sub.7(i)                                                                  H   m.p.: 171-172° C.                 C.sub.4 H.sub.9 (tert.)                                                                 CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              H   n.sub.D.sup.40° : 1.5549          C.sub.3 H.sub.7(i)                                                                      CH.sub.3     C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.9 (sec.)                                                              H   n.sub.D.sup.30° :                 __________________________________________________________________________                                         1.5662                               

EXAMPLE 2 Insecticidal stomach-poison action: Spodoptera littoralis,Heliothis virescens and Dysdercus fasciatus

Cotton plants are sprayed with an aqueous emulsion containing 0.05% ofthe compound to be tested (obtained from a 10% emulsifiableconcentrate).

After the spray coating has dried, the plants are populated with larvaeof the species Spodoptera littoralis (L3 stage), Dysdercus fasciatus (L4stage) or Heliothis virescens (L3 stage). Two plants are used for eachtest compound and insect species. A morality count is made after 2, 4,24 and 48 hours. The test is carried out at 24° C. and 60% relativehumidity. In this test, the compounds of Example 1 are very effectiveagainst larvae of the species Spodoptera littoralis, Dysdercus fasciatusand Heliothis virescens.

EXAMPLE 3 Insecticidal stomach poison action against Leptinotarsadecemlineata

The method described in Example 2 is repeated, using potato plantsinstead of cotton plants and larvae of the species Leptinotarsadecemlineata in the L3 stage. In this test also, the compounds ofExample 1 are effective against larvae of the above species.

EXAMPLE 4 Action against plant-destructive acarids (mites) Tetranychusurticae (OP-sensitive) and tetranychus cinnabarinus (OP-tolerant)

16 hours before the test for acaricidal action, the primary leaves ofPhaseolus vulgaris plants are infected with an infested piece of leaffrom a mass culture of Tetranychus urticae (OP-sensitive) or Tetranychuscinnabarinus (OP-tolerant). (The tolerance refers to the tolerance todiazinone). The treated, infested plants are sprayed with a testsolution containing 400 or 200 ppm of the compound to be tested. A countof the number of living and dead imagines and larvae (all mobile stages)is made under a stereoscopic microscope after 24 hours and again after 7days. One plant is used for each test substance and test species. Duringthe test run, the plants are kept in green-house compartments at 25° C.

In the above test, the compounds of formula I are effective againstadults and larvae of the species Tetranychus urticae and Tetranychuscinnabarius.

EXAMPLE 5 Action against ectoparasitic acarids (ticks: Rhipicephalusbursa (imagines and larvae), Amblyomma hebraeum (♀ imagines, nymphs andlarvae) and Boophilus microplus (larvae, OP-sensitive and OP-tolerant)

The test organisms employed are about 50 larvae, about 25 nymphs orabout 10 imagines of each of the tick species Rhipicephalus bursa,Amblyomma hebraeum and Boophilus microplus. The test organisms areimmersed briefly in an aqueous emulsion or solution containing 0.1, 1.0,10, 50 or 100 ppm of the respective compound. The emulsions or solutionsin test tubes are then absorbed by cotton wool and the wetted testorganisms are kept in the contaminated tubes. A mortality count at eachconcentration is made after 3 days (larvae) and 14 days (nymphs andimagines).

Compounds of the formula I are effective in this test against larvae,nymphs and imagines of Rhipicephalus bursa and Amblyomma hebraeum andagainst larvae (OP-resistant and OP-sensitive) of Boophilus microplus.

What is claimed is:
 1. A compound of the formula ##STR27## wherein eachof R₁, R₂ and R₃ is hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy,trifluoromethyl or nitro, each of R₄ and R₅ is C₂ -C₄ alkyl, R₆ is C₁-C₆ alkyl, C₃ -C₆ alkenyl or C₃ -C₅ alkynyl, R₇ is C₁ -C₁₀ alkyl, C₃ -C₅alkenyl or C₃ -C₆ cycloalkyl, and R₈ is hydrogen or C₁ -C₁₀ alkyl.
 2. Acompound according to claim 1, wherein R₁ is hydrogen, chlorine,methoxy, trifluoromethyl or nitro, each of R₂ and R₃ is hydrogen orchlorine, each of R₄ and R₅ is ethyl, isopropyl, isobutyl, sec-butyl ortert-butyl, R₆ is C₁ -C₆ alkyl, allyl or propargyl, R₇ is C₁ -C₆ alkyl,cyclopropyl or cyclohexyl, and R₈ is hydrogen.
 3. A compound accordingto claim 2, wherein R₁ is hydrogen, chlorine or trifluoromethyl, R₂ ishydrogen or chlorine, R₃ is hydrogen, each of R₄ and R₅ is isopropyl, orR₄ is ethyl and R₅ is sec-butyl, R₆ is methyl, R₇ is tert-butyl orisopropyl, and R₈ is hydrogen.
 4. The compound according to claim 3 ofthe formula ##STR28##
 5. The compound according to claim 3 of theformula ##STR29##
 6. The compound according to claim 3 of the formula##STR30##
 7. The compound according to claim 3 of the formula ##STR31##8. An insecticidal or acaracidal composition which contains, as activecomponent, an insecticidally or acaracidally effective amount of acompound according to claim 1 and a carrier.
 9. A method of controllinga variety of insect and acarid pests of plants and animals whichcomprises applying an insecticidally or acaracidally effective amount ofa compound according to claim 1 to a locus where said pests are to becontrolled.